3-Amino or amido-2-(1H-indol-3-yl) propanoic acid derivatives

Abstract

Disclosed are compounds characterized by the structural formula: <IMAGE> Various compounds circumscribed by the foregoing formula in which: R is H, CH3 or CH2CH3, R' is H, or <IMAGE> X is H, F or OCH3, Y is H or Cl, and Z is H or <IMAGE> are therapeutically useful as anti-hypertensive agents.

What is claimed is: 
     
       1. 3-Amino or amido-2-(1H-indol-3-yl)propanoic acid compounds characterized by the formula: ##STR21## wherein: R is H, CH 3  or CH 2  CH 3 , R' is H or ##STR22## X is H, F or OCH 3 , Y is H or Cl, and   Z is H or ##STR23## provided that: (i) when X is F; Y, Z and R' are H and R is H or CH 3  ;   (ii) when X is H, Y is Cl, Z is H, R is CH 3  and R' is H; and   (iii) when X is OCH 3  ; Y is H provided further that when Z and R' are H, R is CH 3  ; when Z is H and R' is ##STR24##  R is H and when Z is ##STR25##  R' is ##STR26##  and R is CH 2  CH 3 .   
     
     
       2. The compounds defined by claim 1 in the form of their pharmaceutically acceptable, non-toxic, acid addition salts. 
     
     
       3. A compound as defined by claim 1 wherein X is OCH 3 , Y is H, Z is ##STR27## R is CH 2  CH 3  and R' is ##STR28## 
     
     
       4. A compound as defined by claim 1 wherein X is OCH 3 , Y is H, Z is H, R is CH 3  and R' is H. 
     
     
       5. The hydrochloric acid addition salt of the compound defined by claim 4. 
     
     
       6. A compound as defined by claim 1 wherein X is OCH 3 , Y is H, Z is H, R is H and R' is ##STR29## 
     
     
       7. A compound as defined by claim 1 wherein X is H, Y is Cl, Z is H, R is CH 3  and R' is H. 
     
     
       8. The hydrochloric acid addition salt of the compound defined by claim 7. 
     
     
       9. A compound as defined by claim 1 wherein X is F, Y is H, Z is H, R is H and R' is H. 
     
     
       10. A compound as defined by claim 1 wherein X is F, Y is H, Z is H, R is CH 3  and R' is H. 
     
     
       11. The hydrochloric acid addition salt of the compound defined by claim 10. 
     
     
       12. Methyl 3-amino-2-(5-methoxy-1H-indol-3-yl) propanoate hydrochloride. 
     
     
       13. A method of treating hypertension in an individual requiring such treatment which method comprises administering to such individual an anti-hypertensive amount of a compound of the formula: ##STR30## wherein: R is H, CH 3  or CH 2  CH 3 , R' is H or ##STR31## X is H, F or OCH 3 , Y is H or Cl, and   Z is H or ##STR32## provided that: (i) when X is F; Y, Z and R' are H and R is H or CH 3  ;   (ii) when X is H, Y is Cl, Z is H, R is CH 3  and R' is H; and   (iii) when X is OCH 3  ; Y is H provided further that when Z and R' are H, R is CH 3 , when Z is H and R' is ##STR33##  R is H and when Z is ##STR34##  R' is ##STR35##  and R is CH 2  CH 3 .   
     
     
       14. The method of claim 13 wherein the compound administered is in the form of its pharmaceutically acceptable, non-toxic, acid addition salt. 
     
     
       15. The method of claim 13 wherein the compound administered is further defined in that X is OCH 3 , Y is H, Z is ##STR36## R is CH 2  CH 3  and R' is ##STR37## 
     
     
       16. The method of claim 13 wherein the compound administered is further defined in that X is OCH 3 , Y is H, Z is H, R is CH 3  and R' is H. 
     
     
       17. The method of claim 16 wherein the compound defined therein is administered in the form of its hydrochloric acid addition salt. 
     
     
       18. The method of claim 13 wherein the compound administered is further defined in that X is OCH 3 , Y is H, Z is H, R is H and R' is ##STR38## 
     
     
       19. The method of claim 13 wherein the compound administered is further defined in that X is H, Y is Cl, Z is H, R is CH 3  and R' is H. 
     
     
       20. The method of claim 19 wherein the compound defined therein is administered in the form of its hydrochloric acid addition salt. 
     
     
       21. The method of claim 13 wherein the compound administered is further defined in that X is F, Y is H, Z is H, R is H and R' is H. 
     
     
       22. The method of claim 13 wherein the compound administered is further defined in that X is F, Y is H, Z is H, R is CH 3  and R' is H. 
     
     
       23. The method of claim 22 wherein the compound defined therein is administered in the form of its hydrochloric acid addition salt.